


rebel, you're the sun

by orphan_account



Category: Newsies (1992), Newsies - All Media Types, Newsies!: the Musical - Fierstein/Menken
Genre: Alternate Universe - College/University, Alternate Universe - High School, Alternate Universe - Modern Setting, An Ungodly Amount Of Nicknames, Anxiety, Bisexual Jack Kelly, Bisexual Male Character, Bisexuality, F/F, F/M, Fluff and Angst, Fluff and Humor, Implied/Referenced Child Abuse, Jack Kelly Being an Idiot, M/M, Multi, Past Jack Kelly/Katherine Pulitzer, References to Depression, Summer Vacation, Tooth-Rotting Fluff, Useless Lesbians, also i swear once chapter 2 is up the summary will make sense, chapter 1 is just self indulgent background, i love that that's a tag, idk how long this is gonna be but i have so many fun ideas, like. seriously. an ungodly amount, the jacobs siblings show up in chapter 2!
Language: English
Status: In-Progress
Published: 2020-08-04
Updated: 2020-08-12
Packaged: 2021-03-05 22:54:44
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 6,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25703149
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: She ran off, leaving Jack in a shocked state of confusion, a sketchbook held limply in his hand.So. He was going to stay in lesbian-Katherine's father's condo with her, her maybe-girlfriend, and her maybe-girlfriend's twin brother, whom he was going to have to force to have fun. For a week. In Florida, which, contrary to popular belief, was not New York.What did Jack Kelly get himself into?
Relationships: David Jacobs/Jack Kelly, Sarah Jacobs/Katherine Plumber Pulitzer
Comments: 14
Kudos: 31





	1. baby, you're a wild one

**Author's Note:**

> okay yeah hi i had this idea and had to write it !!
> 
> this is probably the weirdest thing i'm ever going to write but it is highkey inspired by romcoms and such because i am Baby and i just ,, i needed fluff
> 
> though, do heed the tags !! this will also have some Bad Stuff in it (in regards to character backgrounds) but i'll always put trigger warnings in front of chapters!! 
> 
> TRIGGER WARNING: mentions of medication, anxiety, depression, general 'Jack Doesn't Have A Good Time,' sexuality crisis

Meeting Katherine had been the genesis of Jack's life as he knew it.

It all started with Jack quite literally running into her on a skateboard on the first day back to school after Thanksgiving break. The sky above was a brilliant blue, and the leaves on the trees were just starting to change colors. The last of the summer heat was finally wearing off. Jack remembered the chill in the air, specifically; only because he was wearing a new hoodie that his foster mom had gotten him. One that was his favorite shade of blue- cerulean- and had his favorite Vincent Van Gogh quote hand-sewn in beautiful script just above his collarbone on his left side; _"I am seeking, I am thriving, I am in it with all my heart."_

Such a small detail was likely to go unnoticed, but that was alright with Jack. High school was already scrutinizing enough. He didn't need anyone pointing things out and making a fool out of himself for something as simple as personalized words sewn into fabric. He was able to make a fool out of himself well enough on his own, thank you very much.

At least, it sure as hell didn't take him very long to prove it.

One second, he was listening to _Royals_ by Lorde, blasting through his headphones in true 2014 freshman fashion, and the next, he was sprawled out on his stomach on the concrete, with the tell-tale pained yelp from someone on the ground behind him.

He hadn't even gotten to stand up before he felt a bag full of textbooks forcefully dropped onto his back and, yeah, okay, he deserved that, but did he really deserve it from _Katherine Pulitzer?_

Seriously. She was the richest girl in school, taking all AP classes to make sure she was front in line for valedictorian four years ahead. Her $80 backpack likely weighed more than _Jack_ with all of the extra weight added in. Textbook after textbook- _did she not know the school provided lockers?-_ mixed with whatever the hell else girls usually had in their bags. 

Frankly, Jack didn't think he warranted all of that weight trying to crack his spine.

He would have complained more than his groan of pain and frustration, but decided against it once he rolled over saw Katherine sitting on the sidewalk with scraped palms and ripped tights and tears in her eyes.

The only thing she had said to him before stomping away was, _"Fuck you, Kelly."_

There Jack went, pissing off the princess.

This was going to be great.

In their first period- Algebra 1, lucky them- Jack had been assigned to sit next to Katherine. It was only the first day of school after break and his ADHD was already kicking in full swing so, while their teacher, Mr. Snyder, was going over the slope-intercept formula, Jack was drawing a small doodle of himself on a hot pink sticky note. In the doodle, he was shrugging, with a text box over his head. As per usual, his apology was something less than sincere, but better than nothing.

_"sorry, didnt mean 2 run into you. was aiming for Snyder instead :/"_

Katherine was the first one in their algebra class to get in trouble that day, all because she snorted after reading Jack's note.

In retrospect, it wasn't even that funny, but her laugh had caused her to get in trouble, which caused her to blame Jack, which caused them both to receive lunch detention on the first day back, meaning they wouldn't be able to eat with their friends after all.

She never forgave Jack, but that unfortunate incident had led to a five year friendship.

An unlikely friendship, but a friendship nonetheless. 

Katherine was the good girl. The one who freaked out when she got less than a 95% on an assignment, the one who got up every day and did hair and makeup and wore dresses and skirts, the one who brought a packed lunch full of ethically sourced food from local farmers markets and high end grocery stores that sold things like _vegan honey_ and _kale._

Jack, on the other hand, was happy to get at least a 70% on any assignment. He was the kind of guy to bring lunchables to school as a senior and eat them during English class, and regularly show up late with coffee for himself and a Dr. Pepper for his homeroom teacher just to avoid getting in trouble. At least he had somewhat of a sense of style, which was really the only thing he had in common with Katherine- at least, until they dated.

Kind of dated.

Well, it was only for four months during senior year, but those four months barely counted, because all they did was… hang out. They didn't exactly change up their usual agenda. They would sit next to each other in class and at lunch, and ended up at a house after school- who's it belonged to didn't matter, because they both spent an equal amount of time at each other's houses anyway. Sure, they would kiss a few times, but it never really felt like anything… spectacular. To Jack, it felt awkward. To Katherine, it felt... wrong.

It was like kissing a wall. It felt fine, maybe, kinda, but there was no emotional connection. No romance. For the two of them, it was just… an action. They played it up, made it seem better than it really was because, well, they were supposed to be together, right? Everyone assumed it. They couldn't be just friends- they had heard that enough times to make each believe it had to be true. It was almost like they were waiting for someone to just… bite the bullet and break up, or propose, because that's what was supposed to happen, right? For four years, Katherine and Jack had been inseparable. Obviously they would have needed to fast forward and get married and have kids and move to the suburbs and have a yard with a white picket fence and a garden and flower beds and a porch swing, right?

Right?

It's funny how things work out.

One day, Jack missed school. Jack wasn't known to do that- although he wasn't exactly a model student, Jack loved school. He got to light-heartedly annoy teachers and was able to finish assignments, leave class, and work on homecoming posters with the art club. School gave him an outlet to ignore everything going on with the outside world. School was where Katherine was, where Race and Spot and Charlie and all of his friends who made him feel normal were.

He hadn't missed a day in a long time, until that Wednesday. 

Of course, this was concerning for Katherine. Her boyfriend, _her best friend,_ suddenly up and vanished? She had sent him snaps and DM'ed him on Instagram and everything. A few pics of homework schedules, some notes, a few art memes posted on some niche account on Instagram. She even sent him a link to a video of a horse on TikTok, and he didn't even reply to _that-_ but on each platform, Katherine could see that her messages had been delivered, and some had been opened.

Jack wasn't the kind to not reply, unless he was busy... or unless he was seriously going through something.

It had caused her to worry all day. She didn't learn a thing in French class, barely touched her assignment in calculus, and her debate about the implications behind the plot in _The Picture of Dorian Gray_ was less than enthusiastic. But, really, how could she focus on Oscar Wilde when Jack Kelly was suffering through something alone just a mile away?

Had she had the nerve to get in trouble, she would have left the school to run to Jack's place during lunch, but she saved that until after seventh period. As soon as the final bell rang she was jumping out of her seat and racing through the hallway to the front entrance, preparing herself for what was to come.

What would she even say? Would she yell at him for not responding? Would she cry and tell him how worried she was? Would that make him feel guilty? She didn't want him to feel guilty. She wanted him to feel safe and comforted, but God, she was worried.

Katherine was unable to come up with a concrete answer, because, before she knew it, she was ringing the doorbell. 

Really, she should have known better than to assume Jack would be the one to open the door. Instead, Katherine was met face to face with Jack's adoptive mom- Medda Larkin, who was more like a parent than anyone else Jack had ever been in a home with. Katherine had heard the stories of Jack's past foster families, and not many of those stories were good. But Medda had been a turning point for Jack, the summer before freshman year, and watching them turn from awkward and bitter to a loving mother and son duo was one of the best things Katherine had ever witnessed.

"Ms. Larkin! Hi, how are you?" Katherine asked as soon as the door opened.

Her plan to at least look more composed than she felt must not have worked, because Medda had a sympathetic smile on her face, and she gently wrapped an arm around her. She pulled her in for a hug, something she did regardless of how many times Katherine had come over- she saw her as a daughter, truthfully. "I'm doing good, baby. If you're here for Jack, he's upstairs in his room," She murmured as she pulled away, a defeated sigh leaving her lips. "He's… Well, you know how that boy gets when he doesn't have his medication."

Katherine cringed. "Is… Is that all that's going on?"

"Well," Medda started, stepping to the side to let Katherine walk in. She shut the door behind her, hands on her hips as she looked toward the staircase. "There was just an issue with the prescription. His refills will be at the pharmacy in a few days, but he's been… pretty unstable. If you ask me," She paused, thinking of what to say. "If you ask me, he doesn't seem quite like himself- even without the medication. There's something going on in his head and he isn't talking about it."

 _Ah._ There it was.

Jack Kelly, the man who was always willing to lend an ear to any friend in need of a 'vent sesh' had somehow forgotten- _again-_ that he wasn't the only one willing to listen. They'd all tried to lend a shoulder to cry on, but Jack had this… thing, against being vulnerable. A personal vendetta that even Katherine had never been able to understand. Katherine had known Jack since freshman year, and now they were seniors. She had hoped he would have grown out of all of this, but it didn't seem so.

"I… I'll go talk to him," Katherine decided with a determined nod, and gave Medda one last hug before starting toward the stairs. She knew how unpredictable Jack's mood could get without his medication, though Medda hadn't specified which he had run out of. If he had run out of his antidepressants, she was prepared to sit in a dark room and hold him until he was ready to talk. If he had run out of his anti-anxiety medication, she was prepared to sit in a dark room and hold him while he spilled his guts on everything that had been plaguing his mind for the past twenty-four hours.

Either way, she was ready for whatever faced her behind the door.

The walk upstairs felt like it was simultaneously five seconds and five years. Her heart was pounding in her chest. The last time anything like this had happened, Jack had spiraled into a dark place in a matter of minutes, so much so that he missed a week of freshman year and had erased all of his social media presence by the end of the day.

Before she walked into his room, she quickly checked her phone, and--

Okay. All of his accounts were still there. That was... good. Still didn't mean much, but at least he was better than last time.

Katherine took a deep breath before knocking on his door, biting her lip. "Jackie? Baby, hey, it's me," She said softly, but loud enough to be heard behind the big wooden door. "Medda told me you were up here… She told me about your meds, too. Can I come in? We don't have to talk about what's going on if you don't want to, I just… wanna make sure you're okay."

It was a few moments, but the door eventually unlocked. Katherine gave him a few more moments to compose himself before she slowly opened the door, gulping at the sight of it all.

There were clothes strewn all over. The bed was a mess of sheets and blankets and what looked to be a few tubes of acrylic paints. There were half finished canvases all over the floor, and… one bleary-eyed Jack Kelly sitting in the corner of the room, staring blankly over the sea of clutter.

"Jack," Katherine said softly as she approached, pulling off her heels and placing them on the ground. Once she was next to him, she placed a hand on his shoulder, and he crumpled. Just as she had predicted, he maneuvered himself to lie with his head in her lap, tears streaming down his face as he stared at the ceiling. There was so much going on inside his head, she could practically hear the gears turning. What brought this storm of uncertainty was a mystery, but she was ready to be there for him no matter what. 

"Jackie," She murmured, running a hand through his messy curls. "Hey, hey, it's… it's gonna be okay, yeah? You'll be okay. I… I know it might not seem like it right now, but you're so strong, you've been through so much, yeah? What's that thing you always told me-- That Dolly Parton quote, the one about the rainbow?" Katherine paused long enough to look down at him, and was grateful to see that he at least has a hint of a smile on his face. "I don't remember how it goes, but just think of that, you… country-music loving weirdo," She laughed fondly, and it must have been enough to make Jack feel somewhat better, because he gave a barely there chuckle. 

They sat there in silence for a few moments. Jack was letting the last of his tears fall, with Katherine stroking his hair. He took in a few shuddering breaths and wiped his eyes, looking up at her with a sad smile. "Hey, Katie?"

"Yeah, Jack?"

"… I think we need to break up."

A beat of silence.

Another.

Slowly, Katherine took in a deep breath, and nodded her head. "If that's what you think is best for us, for you… then okay. Let's break up."

Jack furrowed his brows, though the expression on his face was one of relief, of confusion, of defeat. "You-- You ain't mad at me?"

"I can't say I'm not upset," Katherine replied softly, then nudged his shoulder, "but I'm not angry. I'd never be angry over this, Jackie. Besides, we were friends beforehand, we can be friends now. You aren't getting rid of me that easily, Kelly."

"I hate you so much."

"You know you love me, asshat."

There were a few moments of silence that followed. Their position never changed- Jack still had his head in her lap, her hand was still combing through those wild curls. Things were… nice. Katherine felt like she could breathe again, so she couldn't imagine how Jack was feeling.

"If- Jack, if you don't mind me asking… Uh, Why did you want to break up?" She asked quietly, looking down at him.

At that, Jack sat up, facing with his back toward her. He rushed his forehead for a few moments and let out a deep sigh, before looking up at the window he was facing- the only thing illuminating the room.

"I love you, Kate. I really do, just… just not the way I should."

"Great way to sound like an angst-ridden teenager in a CW show."

"Shut the fuck up," Jack said with a fond smile, rolling his eyes. "I've been thinkin' on this all day, of course it's gonna sound a little rehearsed. But… Yeah. I just- I feel like we're better friends, I guess? I wanted to be with you, but it just…"

"Feels awkward. Like you're kissing your sister."

"I mean-- gross, but… yeah? I guess?"

Katherine shook her head and huffed, moving to sit behind Jack. She wrapped her arms around his shoulders as a soft sigh left her lips. "You dumbass, you could have told me sooner!"

"And risk losing you? No!" Jack shot back, but leaned into her embrace. "I couldn't… I can't even _think_ about not havin' you. And I didn't wanna risk it," He explained, closing his eyes with a deep sigh.

"Just because we aren't dating doesn't mean we can't still hang out," Katherine murmured softly. "I can't lose my favorite dumbass."

"Wow, I feel so loved."

"I'm serious!" She protested with a whine, and moved to sit next to him, lying with her head on his shoulder. "Is that all that's been bugging you? Don't lie to me, Jackson Francis Kelly."

"First of all, it's 'Francisco.' Get it right," He huffed, nudging her side with his elbow. "Secondly, I… There is somethin' else, but I don't… I don't know yet."

"You know you can tell me anything, right?"

"I know, I know! This is just… I don't know. Big thing. It, uh… kinda hit me last night, and I… I didn't sleep. Had a few panic attacks. Cried in the shower. The usual."

"Jack, honey, I love you, but _maybe_ you need to find a better coping mechanism."

"Stop interrupting, Katie-dear."

"Right. Sorry."

"Anyway," Jack started, clasping his hands together. "Last night. I, uh… I was readin' this thing that Charlie put on his Instagram story, right? It was some article about guys who… like other guys, and Charlie put a little message on the story and said that he, like, related to some of the things, y'know? So I was readin' to… I don't know. Understand what he was talkin' about, I guess. And, uh, while I was readin'... I realized that, um, I've… I've felt some of the things it was talkin' about," He admitted, glancing away.

Katherine took a moment, then took in a deep breath. "Jack… Are you gay?"

"I-- _Fuck,_ Katie, I don't know," He admitted, hiding his face behind his hands as he hunched forward, resting his elbows on his knees. "No? Maybe? I-- I was readin' that thing and it made me realize that- that I've liked dudes before. I've checked other guys out, I've had- fuckin' hell, I've had dreams about kissin' other guys, but- but I've had the same dreams about girls, y'know? And I've had girlfriends before that I genuinely liked and--"

"You might be bi," Katherine cut in, rubbing his back. "You know… you might not like just guys, or just girls. You might just like… everyone. Sexuality is fluid, right? I mean... Well, for instance, I'm pretty sure I'm not straight either. But we don't have to know juat yet," She murmured, a gentle smile on her face. "That being said, I can't tell you your own sexuality. That's something you need to figure out alone, but don't forget that you have /tons/ of people who are here to listen and accept you, okay? No one is going go think any different about you. I promise. We love you, Jack."

Jack didn't say anything after that. Katherine could see the look on his face- somewhere between confusion and fear, but she watched that expression melt into relief. Acceptance. Jack nodded and leaned against her, and she pulled him close. 

They stayed like that for a long time, silently holding each other until Katherine had to go home for dinner. As she stood, she pressed a gentle kiss to Jack's forehead, looking into his eyes. "Remember to call me, Jackie. No matter what. I'm here for you, okay? I'm always here to listen," She murmured, giving him one last gentle smile before walking through the room. She slipped her heels back on and hurried downstairs, leaving Jack in his room alone.

Surprisingly, Jack came downstairs for dinner. That wasn't exactly typical- usually on days like this, Jack didn't eat unless Medda brought him food, and still, usually he only picked at his plate for hours until everything got cold and too gross to eat.

But not tonight. 

Tonight, Jack sat at Medda's side and ate. They didn't talk, but that was okay. They didn't need to. He finished his food wordlessly, after about twenty minutes. After washing his dishes, Jack beaded for the stairs, but hesitated. He stood there, frozen, eyes on the ground for a long moment, until Medda's voice rang through the silence.

"Jackie? Baby, are you alright?"

 _Was_ he alright? That was a good question.

"...I love you, Ma," Jack said finally, turning on his heels to face her, though his gaze stayed glued to the ground. "A lot."

"I love you too, hunny… We don't need to talk about this tonight, okay?" She said softly, shooting him a smile. "We can talk about whatever is bothering you tomorrow. Or another day, whenever you feel like it. Just… let me know, and I'll be here for you, okay?"

"I-... Okay. Thanks."

With that, Jack crossed the room and gave her a big hug, though he quickly pulled back and hurried upstairs. This was going to be a long night. 

Hopefully Charlie didn't mind sending him more articles.


	2. i can feel it now

**Summary for the Chapter:**

> _He used a lot of words, but Jack was stuck hanging onto the end of each one, mesmerized by the way he spoke, the way he was able to use his words._
> 
> _Maybe this trip wouldn't be so bad after all._

**Notes for the Chapter:**

> TRIGGER WARNINGS; none. pure fluff. just straight up fluff. but maybe not straight

Jack was happy.

Happy. Yeah. Jack hadn't been this happy in years.

Charlie was a big helper in that decision. He was the next one that Jack told, and was able to offer a little bit more insight. After all, Charlie was also a guy who liked guys, and he took the time to explain his experience to Jack and helped Jack put what he was feeling into words.

Truthfully, Jack should have known before now. All of those years averting his eyes in the locker rooms after soccer practice, even when it was just him inside. All of those years spent lying on the floor or on a couch when he went to a friend's house because he felt ashamed to share a bed. All of those years that Jack felt such a heavy feeling in his chest, a guilt he could never understand before, when he locked eyes with a boy and blushed.

But now Jack had a support system. A small group of people who still loved him for who he was, a small group of people that didn't tell him to pick a side or didn't assume he was just slowly coming out as gay. 

No, now, Jack was happy.

That happiness, the happiness that finally came with accepting the truth that had always been there, lasted for quite a while. It lasted past Christmas break, when he and Medda went to Colorado and Jack was able to flirt with a guy he didn't know for the first time ever.

It lasted past the spring semester, when he and Katherine sat down between both of their families at dinner and opened matching acceptance letters from NYU, where they would be majoring in studio arts and journalism, respectively.

It lasted past their high school graduation, something Jack never thought he would make it to. It lasted all the way into their first summer as real adults, real (almost) college kids.

Summer.

Summer was good. Summer meant no responsibility, usually- but not when Jack was going to college in less than two months and needed money. He had gotten a job at some small little craft store, reminiscent of a Hobby Lobby but without the wacky religious overtones. It was stuck in an outlet mall, right down the sidewalk from a little boutique that Katherine worked at, which meant that the both of them were able to eat lunch together when their schedules coincided.

This, of course, did not stop Katherine from coming into the store when their schedules didn't work out together.

"Jackie, c'mon, it's only for a week!"

"Yeah, Kath, but that's a week without work. A week without money. If you have forgotten, my dad ain't a bigwig named Joseph Pulitzer," Jack explained with an exasperated sigh, shaking his head as he continued stocking sketchbooks onto the shelves. 

Jack loved Katherine. She was the best friend he had ever had- of course he loved her.

But sometimes, she was a special breed of annoying that Jack just couldn't escape.

Katherine was leaning against his cart, sipping at a cup of lemonade she'd gotten around the Sonic across the street. For someone who didn't even work here, she sure did make herself at home with the inventory. "See, but that's the thing! Your dad--"

_"--I ain't got a dad--"_

"--isn't Joseph Pulitzer, but mine is! Which means that you're not going to have to pay for anything!"

Jack turned to look at her, raising a brow with a bored look. "Seriously? Kath, really, I love you, but--"

"No, Jack," Katherine shot him a look and crossed her arms. "No. This is something I want to do for you, since you've been such a great friend to me for so long. I love you, and I want you to come with me so we can have a relaxing week on the beach in Florida before we have to be big kids for four more years. Please?"

"No."

"Please? Please, please, please? Let me be a good friend? Please, with a cherry on top? Please? Jack, _please?_ Please, please, please?"

Jack took one more look at her face, and knew he wasn't going to win this. "...Fine! Fine, okay. Yeah. You win," Jack muttered in a huff, but he couldn't help the bemused grin on his face at her excited squeals. "Okay. Okay! Okay, _cool it_ \-- Kath, my love, quiet down, will ya?"

"I love you!" Katherine squeezed her arms around Jack's torso, smiling wide and shaking him. "It's gonna be so much fun! Oh, and, also-- I should tell you, my future roommate and her twin brother are coming too. She and I have been talking and we, uh, might be dating? Oh- by the way, I think I'm a lesbian. Figured it out last week, forgot to tell you. Anyway, her brother is coming along and could really use a friend because he's kind of nerdy and doesn't do much aside from sit inside and read and do smart people things and since you're dumb and know how to make people have fun, you're going to help him get out of his shell while me and his sister get to know each other! You're doing all of us a huge favor, thank you!"

With that, Katherine ran off, leaving Jack in a shocked state of confusion, a sketchbook held limply in his hand.

So, he was going to stay in lesbian-Katherine's father's condo with her, her maybe-girlfriend, and her maybe-girlfriend's twin brother, whom he was going to have to force to have fun. For a week. In Florida, which, contrary to popular belief, was not New York.

What did he get himself into?

That question continued racing through his mind the rest of the week as he prepared for the trip. According to Katherine, the trip was all expenses paid- but Jack still packed about five hundred, just in case. And, yeah, maybe that was his entire last paycheck, but he wasn't going to be that guy and make his rich ex-girlfriend-slash-best friend pay for everything. Medda wouldn't even let him help with buying groceries that week. She insisted that Jack needed to save his money to go have fun with his friends, but Jack still felt bad about the whole 'people are spending money on me' thing.

Especially since Katherine was paying for two other people to go, too.

Two people that neither of them knew very well.

There was Sarah, Katherine's roommate at NYU. They'd been talking to each other before the semester even started, having met online in an Instagram group chat for future NYU students, apparently. Katherine seemed to like her a lot, and more than in just a friendly way. Jack had never seen Katherine look so head over heels for anyone, so he was happy for her, and according to Katherine, Sarah was like an angel on Earth. Kind and funny and beautiful and smart- smart enough to major in clinical psychology, something that Jack would never be intelligent enough to do. He felt a bit… intimidated, but if Katherine liked her, then she had to be a pretty great gal.

Sarah had a brother. Jack didn't know much about him, other than the fact that his name was David and he was an upcoming English major. He was, as Katherine put it, a total bookworm who didn't party or do normal teenager stuff. He didn't get into any trouble, like, ever, and was, quite frankly, the exact opposite of Jack- at least from what he knew about the guy.

Jack hadn't even seen a picture of the guy, yet Katherine was convinced that he and David would be besties.

All of Jack's anxieties culminated the day before the plane ride. Katherine and Sarah had set up a brunch for the four of them, just so they could all get together and meet before the trip. Jack was feeling a bit better about everything with that in mind- at least Sarah and David wouldn't be total strangers, but Jack was still a bit worried about going on vacation with two people he didn't really know. 

Unfortunately, Katherine was still in her 'adventurous heiress' phase, so she apparently didn't see the problem with it.

Maybe that was why her favorite character on _Schitt's Creek_ had been Alexis.

Oh, God.

Jack and Katherine made it to the cafe first. He could definitely tell she was excited- she had done her hair and makeup, was wearing a pair of heeled boots, and had on a light pink, flowy dress. He had seen something on Instagram about the style she was trying to emulate- whatever the fuck a 'cottagecore lesbian' was- but she looked gorgeous, as per usual.

Jack, of course, was much more toned down. He was in a pair of skinny jeans and some beat-up black converse. His black t-shirt was tucked loosely into his jeans, and he had a short sleeved navy button up with floral designs on over it- as well as a beaded necklace of some sort, hidden underneath the layers. The sleeves were cuffed. The jeans were cuffed. Katherine had correctly called him out on every single bisexual stereotype he was showing off as soon as she saw his outfit, but, really, what could Jack say? He thought it looked nice.

Besides, looking nice was important for first impressions.

He and Katherine slid into one side of the booth near the back corner, explaining to the waitress that they were waiting for two others to show up as well. Once they were alone, Jack tapped on the table with a deep sigh and looked out the window.

Maybe he zoned out, maybe he didn't, but all he knew was when he was finally brought back to the present, it was by Katherine sharply nudging him in the ribs with her elbow.

"Ow! You bitch, what was--"

"Shut up! Jack, she's- Look at her," Katherine rushed with a whisper, and Jack looked up, and--

Oh, fuck.

He saw straight past Sarah, but what he saw was… wow.

A boy, about as tall as his sister- maybe even taller. He was definitely taller than Jack, that was for sure. His dark hair was parted on the side and swooped up away from his forehead, and he had gorgeous hazel eyes. He was wearing something pretty chill- a simple white t-shirt and jeans, with a plaid button up thrown over it. He looked so plain, but… he pulled it off in a way Jack would never understand. There was nothing particularly striking about him. No scars that Jack could see, no wacky little beauty marks… nothing that made him look out of the ordinary, but somehow he still managed to take Jack's breath away at first sight.

He was pretty sure he had the same look on his face toward David as Katherine did toward Sarah, though. Just by glancing to the side, he could see she was in awe of the woman walking toward her. If heart eyes were a literal thing, her face would be right next to the definition in the dictionary.

That was when Jack finally looked up and saw why.

The Jacobs siblings must have been models in a past life, holy _fuck_. Sarah was wearing heeled boots, and had on brown checkered pants that were cinched at the waist but loose around the leg. Tucked into her belt was a white turtleneck, though the sleeves were practically nonexistent, cutting in at the end of her collarbone. Her makeup was simple, but dark and bold- unlike Katherine's own soft pink fantasy look she had going on. She looked like a goddess, or like she just walked off of the set of a Dead Poets Society remake where she played the main character at an all girls boarding school… or something like that.

They approached the table fairly quickly. Sarah, presumably, had a shy smile on her face as she made eye contact with Katherine, who gave an awkward little wave. That shocked Jack; he had never before seen Katherine look so… nervous. She must have really liked her.

"Hey, guys," Sarah said with a smile as she slid into the booth- next to the wall, right across from Katherine. She shot her a look, which told Jack that clearly something was going on between them, before turning to face him and holding a hand out. "Sarah Jacobs. I've heard a lot about you."

"Jack Kelly, at your service. Knowing Katherine, what you heard ain't very good," Jack shot back with a toothy grin, but shook her hand nonetheless. She had a strong handshake. Jack knew immediately not to fuck with her.

He grinned as he pulled his hand away, then held it out to David. "You're Davey, right?"

"David. My name is David," He shot back, a little defensively, and stared at Jack's hand for just a fraction of a second too long before taking it and giving it a quick shake. 

Okay, Katherine had warned him about David being a bit stiff, but this was totally not what Jack was expecting.

He pulled his hand away and held them up in surrender, a smug grin on his face. "Sorry 'bout that. You ain't really a nickname guy, huh?"

"Don't let my brother ruin the fun," Sarah cut in, nudging David's shoulder with her own. "He's just grumpy because he wants to stay here and study instead of go on a trip. Like a _freak_."

"Sarah, you really have to say that in public?" David asked in a low voice, barely audible above the soft music in the cafe, and suddenly all Jack could think about was the fact that David's voice was that perfect mix of rough snark and soft embarrassment and- fuck, Jack really needed to stop while he was ahead.

"It's for your own good!" Sarah protested, and smiled at him. "This is gonna be good! Really good. For both of us," She shook his arm, then cast a glance toward Katherine.

"Mhm. Sure. Whatever you say, Saz."

Sarah shook her head, but didn't say anything else. She turned back to Katherine, who still seemed to be a little awestruck, and soon began talking about something else- something about their dorm building, something that David and Jack wouldn't be able to participate in.

Jack clasped his hands together and looked up at David with an awkward grin. "So, uh… Kath tells me you're gonna be an English major, huh? You must be real smart."

"Intelligence has nothing to do with it," David replied simply.

Great. This conversation was getting nowhere fast.

"Really? 'Cause I know I'd never be able to do that. I ain't smart enough with words to do somethin' like that," Jack muttered with a forced laugh, trying to ease the tension, but then he looked up and saw that David was staring at him. His gaze was so intense, like he was trying to see into Jack's soul, and just the thought made his cheeks heat up a little. 

"What's your major?"

"I-- What?"

"Your major?" David repeated, a curious look on his face. "What are you studying?"

"...Studio arts," Jack admitted slowly, looking back at David with a critical expression. "I know, I know, it ain't exactly a 'money making' profession, but--"

"No, no, you're right. But it _should_ be," David offered, then leaned forward a bit. "See, I'm going into academics. I'm studying English because it'll give me the tools I need to communicate effectively with others. It's tactical, it'll help me get far. But, you?" He paused, grinning, and Jack had never seen a more beautiful sight. "You're actually creating. You're making something that can- no, _will_ \- elicit an emotion. You're communicating and connecting with others without ever using words, and you're making it into something practical. You're making a statement piece that will make someone feel something. And, to me, that should warrant a better paying expected income. Don't you think?" David finished, leaning back in the booth with his arms crossed.

Holy _shit._ Did Jack just fall in love? He was pretty sure he just fell in love.

It took him a moment to think of an answer. David seemed extremely articulate, put together. He seemed to know exactly what to say without a second thought, seemed to have a brain wired for fast paced conversations. He seemed like the kind of kid to be on a debate team, or the kind of person to know a lot about everything without ever having to reread something more than twice- the polar opposite of Jack, in that regard.

There was a reason that Jack hadn't chosen something more academically inclined to major in, aside from his main hobby being art in general. Had he chosen something more taxing, Jack wasn't sure he would be able to keep up. He had always struggled when put in front of a textbook or a document, and he had the grades to prove that, but when put in front of a canvas? Jack flourished. He was able to tell wild stories with just a brushstroke, able to say everything he couldn't put into words with colors and designs.

He couldn't do that with his words, not like David could.

"Uh-- I mean, yeah. 'Course I agree. Who don't want more money?" Jack asked with a chuckle, but cringed ever so slightly. "But don't sell yourself short, pal. It takes a lot 'a skill to be able to do what you're gonna do. So, are you hopin' to, like… be an English teacher or somethin'?"

"Nah. I'm not cut out for teaching. I'm more interested in being an editor, actually," David explained with a soft grin. He seemed to soften up a bit, hold his head a little higher than before- especially as he began talking about why editing was what he wanted to do. He used a lot of words, but Jack was stuck hanging onto the end of each one, mesmerized by the way he spoke, the way he was able to use his words.

Maybe this trip wouldn't be so bad after all.

**Notes for the Chapter:**

> WE FINALLY HAVE THE JACOBS SIBLINGS IN APPEARANCE!!
> 
> what'd y'all think? is the trip gonna be smooth sailing, or do you think something is going to happen? how are we liking Jack "Disaster Bi" Kelly? what about Kath and Sarah, our favorite cottagecore/dark academia wlws?? and DAVEY !! my baby boy Davey and his inability not to rant when he finds somethin he's passionate about!!
> 
> i would really love to hear y'alls feedback but i am so excited to keep writing this !!!!
> 
> also; shoot me an ask over at @we-are-inevitable on tumblr if you're up for it !! i take drabble requests, and questions/comments about this fic are appreciated !!!!

**Author's Note:**

> i really hope you guys enjoy this- chapter 2 will be up soon! pls comment if you wanna see more!!
> 
> also, chapter 2 picks up after their senior year, so that's when the Jacobs siblings make their appearance!
> 
> i dont really have a specific reason for wanting to write this chapter with Jack and Katherine, aside from wanting to set up the nature of their friendship for the rest of the fic, but i hope that ?? it was at least somewhat enjoyable!! mwah
> 
> come say hi on tumblr! i take drabble requests on @we-are-inevitable !!


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